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Merck

I2892

Ifenprodil (+)-tartrate salt

NMDA antagonist

Synonyme(s) :

α-(4-Hydroxyphenyl)-β-methyl-4-benzyl-1-piperidineethanol (+)-tartrate salt

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A propos de cet article

Formule linéaire :
(C21H27NO2)2 · C4H6O6
Numéro CAS:
23210-58-4
Poids moléculaire :
800.98
NACRES:
NA.77
PubChem Substance ID:
24278826
UNSPSC Code:
12352200
EC Number:
245-493-5
MDL number:
MFCD01529999
Quality level:
200

Principaux documents

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Nom du produit

Ifenprodil (+)-tartrate salt,

storage temp.

room temp

Quality Level

200

SMILES string

OC(C(O)C(O)=O)C(O)=O.CC(C(O)c1ccc(O)cc1)N2CCC(CC2)Cc3ccccc3.CC(C(O)c4ccc(O)cc4)N5CCC(CC5)Cc6ccccc6

InChI

1S/2C21H27NO2.C4H6O6/c2*1-16(21(24)19-7-9-20(23)10-8-19)22-13-11-18(12-14-22)15-17-5-3-2-4-6-17;5-1(3(7)8)2(6)4(9)10/h2*2-10,16,18,21,23-24H,11-15H2,1H3;1-2,5-6H,(H,7,8)(H,9,10)

InChI key

DMPRDSPPYMZQBT-UHFFFAOYSA-N

Gene Information

human ... GRIN1(2902), GRIN2A(2903), GRIN2B(2904), GRIN2C(2905), GRIN2D(2906), GRINA(2907)

Catégories apparentées

General description

Ifenprodil is a phenylethanolamine, which stimulates blood circulation. It has anticonvulsant and antinociceptive properties. Ifenprodil is used to treat posttraumatic stress disorder, cerebrovascular diseases and peripheral arterial obliterative disease. It blocks G protein-coupled inwardly-rectifying potassium channels (GIRKs) and interacts with α1 adrenergic, N-methyl-D-aspartate and serotonin receptors.

Application

Ifenprodil (+)-tartrate salt has been used:
  • to test the action in a KCl-induced cortical spreading depression (CSD) animal
  • to study its effects on electrophysiological properties and spontaneous spikes in neocortical pyramidal cells
  • to investigate its therapeutic effects

Biochem/physiol Actions

NMDA antagonist acting at the polyamine site; neuroprotective agent; α-adrenergic central and peripheral vasodilator; α2 adrenergic receptor ligand.

Features and Benefits

This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Glutamate Receptors (Ion Channel Family) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Classe de stockage

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificats d'analyse (COA)

Lot/Batch Number
0000479050
0000479050
0000445537
0000350693
0000350693

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Consulter la Bibliothèque de documents

Involvement of NMDA receptor subtypes in cortical spreading depression in rats assessed by fMRI
Shatillo A, et al.
Neuropharmacology, 93, 164-170 (2015)
B L Chenard et al.
Current pharmaceutical design, 5(5), 381-404 (1999-04-24)
In the late 1980s, a new class of N-methyl-D-aspartate (NMDA) receptor antagonists, exemplified by the phenylethanolamine ifenprodil (1), was identified. Initially, the mechanism of action of ifenprodil was a mystery as it was not a competitive antagonist at the glutamate
Ifenprodil and SL 82.0715 are antagonists at the polyamine site of the N-methyl-D-aspartate (NMDA) receptor.
C Carter et al.
European journal of pharmacology, 164(3), 611-612 (1989-05-30)
Austen J Milnerwood et al.
Neurobiology of disease, 48(1), 40-51 (2012-06-07)
We recently reported evidence for disturbed synaptic versus extrasynaptic NMDAR transmission in the early pathogenesis of Huntington's disease (HD), a late-onset neurodegenerative disorder caused by CAG repeat expansion in the gene encoding huntingtin. Studies in glutamatergic cells indicate that synaptic
Matthew K Brittain et al.
Neuropharmacology, 63(6), 974-982 (2012-07-24)
Glutamate-induced delayed calcium dysregulation (DCD) is causally linked to excitotoxic neuronal death. The mechanisms of DCD are not completely understood, but it has been proposed that the excessive influx of external Ca(2+) is essential for DCD. The NMDA-subtype of glutamate
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